Synthesis and properties of fluorine-containing heterocyclic compounds. V. Trifluoromethyl-1,8- and 1,10-phenanthrolines |
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Authors: | Edwin B Nyquist Madeleine M Joulli |
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Institution: | Edwin B. Nyquist,Madeleine M. Joullié |
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Abstract: | The condensation of ethyl trifluoroacetoacetate with various heterocyclic amines yielded 2-(trifluoromethyl)phenanthrolin-4-ones. The structures of these compounds were established from a study of their infrared and ultraviolet spectra. Substituted phenanthrolines were prepared by nucleophilic attack on a chlorophenanthroline. The oxidation of 5-methoxy-2-trifluoromethyl-1,10-phenanthroline yielded an o-quinone which was treated with typical quinone reagents. A molecular orbital calculation was carried out in an attempt to explain the ease of reduction of the 1,10-phenanthroline system and the colors of the reduced compounds. |
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